I Gave Her a Free Pass for 5 Nights

Ally

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Hello,

Ally and I had been dating for a little under a year. Things were going great, we had just recently moved in together, life couldn't have been better. And then I fucked up. I got pulled over heading home from the bar and got a DUI. When all was said and done I ended up with a couple of grand in fines and a week in jail. I wasn't exactly thrilled about spending a week in jail but I got work release, so I'd just have to spend the night in county lockup. I didn't think it was that big of a deal, Ally on the other hand was devastated. We hadn't spent a night apart since the first couple of months that we had been dating. She doesn't know how she's going to sleep without me for a whole week. I try to calm her down the best I can and tell her it will be ok.

I had about a month and a half from the time I was sentenced until I actually had to go on and do my time. Life went on like normal. While we were having sex she would make comments like how much she was going to miss fucking me and saying she'd have come come see me on my lunch break and fuck me in my office. One night I tell her I'll just have to give her a hall pass for the week. I can tell she's intrigued but she says she wouldn't do it, she loves me too much. I don't really press the issue because she doesn't seem like she's 100% on board. Life goes on like normal for the next few weeks but every once and a while while we're having sex she'll bring up the hall pass to tease me and ask me things like, "So you won't mind if I have some other guy over here fucking my brains out in our bed while you're locked up." I play it cool and tell her maybe it might be kind of hot, but you'd definitely have to get me some pictures or video. She can tell by how hard I get that I absolutely think it would be hot.

The fateful day finally comes and I have to go into jail. The first night in she couldn't drive me because she had to work. No big deal, I take an uber in and report in. I show up, text my girl goodnight, turn in my personal belongings, get booked in and am escorted into my new digs for the next seven days. It's really not so bad but my bed is uncomfortable as shit. I sleep for a few hours and get ready for my day. When I check out to head back to work she's already waiting in the parking lot. We talk about our first night apart, how awful it was and how neither one of us got much sleep. She takes me into work and I go about my day.

We were texting back and forth all day and I don't remember who brought up the hall pass but I think it got real for her and all of the sudden she is totally against it. When she picks me up to take me back to jail that night she starts asking me about it and I reiterate how I think it would be kind of hot, spice things up a little bit. She gets upset and thinks that I don't value her at all and can't believe I would say that. So I tell her just to forget it, I don't want it to cause any problems. She tells me, "No, I can tell you want me to do it so I am going to get fucked tonight." I try and talk her out of it but she's not having it now. She asks if I would be mad if she fucked her ex and I tell her absolutely, I don't want you to fuck your ex because there's feelings involved there. We've arrived at the jail and I want to sit there and talk this out but unfortunately I don't have that luxury right now and I have to check in for the night. I kiss her goodbye and tell her I love her. She says she loves me too but she also says, "I'm going to be getting off tonight and it won't be from your dick so you can sit in there tonight and think about that." On my way in I text her again to tell her that I love her and tell her to be safe. She just texts back "I will."

I didn't sleep much that night, it's nerve wracking to wonder what is going on in the outside world while you're locked up with no access to your phone until 10am. I got a few hours of sleep but mostly I stare at the ceiling wondering if she's actually going through with it, or if she's just trying to punish me. 10am finally rolls around so I get up and get ready for work. They finally let me out around 10:45 and I get to my phone. I turn it on and there are no notifications. I was both relieved and worried at this point. I go outside to wait for my uber and I give her a call. We're talking but I'm not bringing it up. Eventually she asks if I want to know how last night went so I said sure.

She tells me she did it, but can't talk about it right now because she's at work. I can't tell if she's serious or just trying to see how I'd react. I hang up and text her to ask for details. She said after she dropped me off she called up a girlfriend of hers and told her she needed to get laid. Her friend was heading to a house party so Ally went and joined her. Her friend asked if she was feeling ok because she knew that her and I were dating, said friend had just been over to our place recently for a party, and that this was really out of character for Ally. Ally said "yeah everything is fine, I was just in jail so she wanted to get laid tonight. Like a good friend she took my girlfriend to this party and introduced Ally to one of her friends named Mike. Ally told me her and Mike had a few drinks, played some beer pong and talked for about an hour.

Eventually she asked Mike if he wanted to get out of there so he took her back to his place. She said as soon as they walked in the door he pushed her up against the wall and started tearing her clothes off. She blew him in the kitchen for a few minutes and then he bent her over the couch and started fucking her. She told me he was really aggressive and rough with her, she had a really good time but she didn't come. Then she asked if, "I was proud of her." I told her she had no idea, that is sexy as fuck and that I'd be walking around hard all day long at work. I asked if she had any pics and she said maybe... Eventually she sent me a video of her getting fucked doggy style on someone else's bed. I told her I about came right then and there. But then I noticed something off about the video, it was geotagged in another city. It was a video of her fucking an ex. I call her out on this and she came clean and told me everything she said was true, she was just mad at me and didn't take any pics or video. She said she feels bad now because she did it to get back at me and didn't care if she got any pics or video. I was a little upset. Not so much that she fucked some guy last night, or that she didn't get any pics, although I was a little bummed by this, but that she did it because she was mad at me. I didn't let her know I was mad though, and just let her know that I understand why she was mad and I still thought it was hot as fuck.

The day went on, I was pretty busy at work but still made a point to text her as much as I could and let her know that everything was ok. Eventually she said she still had five more days on her hall pass and since she already fucked another guy I should at least get a video out of the deal. I was floored, I didn't think she'd jump back in the saddle that quick. She asked if I wanted her to go fuck the same guy or if she should find someone new. I told her that it was entirely up to her so she text me back and told me she was trying online sites and was going to get to work. A couple of hours later it was time for me to go back to jail. She came and picked me up, gave me a long kiss and then handed me her phone.

She had three guys lined up and she just placed her first ad, and she told me I got to pick who was going to fuck her tonight. She had a guy that looked a lot like me, just a little younger, a taller lanky guy and a black guy. I wasn't sure if I was ready to see my sweet loving girlfriend get fucked by a black guy so I vetoed him and eventually settled on the younger guy. I looked through their conversation and damn, I didn't know my girlfriend could be so smooth. He seemed like an alright guy so she said ok, you text him and convince him to come and fuck me and take some videos. He wasn't 100% on taking videos, I felt like I might have been losing him.

We had just arrived back at jail so unfortunately I had to go in. She took her phone back and called him and gave me a kiss goodnight while she was talking to him. It took forever to get checked in that night and right before I shut my phone off and turned it in for the night I get a text. "He's coming over babe ??" That night was one of the longest nights of my life. I don't think I slept at all I just laid there all night staring at the clock waiting for 10am knowing that my girl was getting fucked at our apartment on our bed and I was absolutely powerless to do anything about it. I had moments when I wished I could call her and tell her not to do it but there was literally nothing I could do. She was getting some dick and I was sitting there in jail jacking off powerless to stop it.

Mercifully the clock finally strikes 10. I get ready for work and finally get to my phone. Turn it on and.. no notifications. Wtf why didn't she send me anything? Did she not go through with it? Is everything ok? She was in class so I text her good morning and ask her how last night went. I get a reply as I load into my uber, I can barely contain myself. I look down at my phone and it's a video. She's sucking his cock and swallows his cum. Holy fuck this was the hottest thing ever. We didn't talk about no swallowing so I guess I can't be mad. She says she has three more videos but I can't have them yet, she feels like teasing me.

She sends me a video every few hours. First one she's laying down getting fucked missionary and it's shot from her POV. She makes sure she gets a good view of his dick sliding in and out of her pussy. I beg for more but she makes me wait. Next video she is on top riding him and this time he is holding the camera/phone. It's a great view I definitely picked the right guy, dude knows what he's doing with a camera. Last video she sends me right before she picks me up for the night is her getting fucked doggy style on my side of the bed, right where I sleep. Definitely the hottest porn I've ever seen.

On the way to the clink later that night I tell her I have to rescind her hall pass because I'm not going to get any sleep. She agrees and promises me she won't fuck anyone else until I get out of jail. She kept her word and we get off to those videos every night, best investment ever!